#3: The Outlaw Josey Wales
If the Dollars Trilogy brought the antihero character to town, The Outlaw Josey Wales helped it kick down the door.
A box office success, this revisionist Western gave Clint Eastwood another opportunity to impress audiences as director and star. Now seen as a hallmark of his directorial style, the film dove into themes of morality, redemption, and justice. Benefitting from a script filled with iconic lines, The Outlaw Josey Wales proved to be a turning point in how Eastwood was perceived as a filmmaker. As a matter of fact, none other than Orson Welles praised the film and hailed the director as “one of America’s finest.”